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ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE IMINES WITH ACROLEIN CATALYZED BY L-PROLINE AND ITS DERIVATIVES
http://hdl.handle.net/10091/13267
http://hdl.handle.net/10091/13267770f4857-e421-4b29-b5f1-8cdd4c497b55
| 名前 / ファイル | ライセンス | アクション |
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ACR_Azomethine_Imine-6-7-10-revised.pdf (792.4 kB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||||||||||||||
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| 公開日 | 2011-10-12 | |||||||||||||||||
| タイトル | ||||||||||||||||||
| タイトル | ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE IMINES WITH ACROLEIN CATALYZED BY L-PROLINE AND ITS DERIVATIVES | |||||||||||||||||
| 言語 | ||||||||||||||||||
| 言語 | eng | |||||||||||||||||
| DOI | ||||||||||||||||||
| 関連識別子 | https://doi.org/10.3987/COM-10-11967 | |||||||||||||||||
| 関連名称 | 10.3987/COM-10-11967 | |||||||||||||||||
| 資源タイプ | ||||||||||||||||||
| 資源 | http://purl.org/coar/resource_type/c_6501 | |||||||||||||||||
| タイプ | journal article | |||||||||||||||||
| 著者 |
Suga, Hiroyuki
× Suga, Hiroyuki
× Arikawa, Tadashi
× Itoh, Kennosuke
× Okumura, Yukihisa
× Kakehi, Akikazu
× Shiro, Motoo
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| 信州大学研究者総覧へのリンク | ||||||||||||||||||
| 氏名 | Suga, Hiroyuki | |||||||||||||||||
| URL | http://soar-rd.shinshu-u.ac.jp/profile/ja.HmShyVfp.html | |||||||||||||||||
| 信州大学研究者総覧へのリンク | ||||||||||||||||||
| 氏名 | Okumura, Yukihisa | |||||||||||||||||
| URL | http://soar-rd.shinshu-u.ac.jp/profile/ja.gNDVgpAF.html | |||||||||||||||||
| 出版者 | ||||||||||||||||||
| 出版者 | The Japan Institute of Heterocyclic Chemistry | |||||||||||||||||
| 引用 | ||||||||||||||||||
| 内容記述 | HETEROCYCLES. 81(7):1669-1688 (2010) | |||||||||||||||||
| 書誌情報 |
HETEROCYCLES 巻 81, 号 7, p. 1669-1688, 発行日 2010-07-01 |
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| 抄録 | ||||||||||||||||||
| 内容記述 | 1,3-Dipolar cycloadditions between acrolein and various N,N'-cyclic azomethine imines in the presence of L-proline and its derivatives as organocatalysts were investigated. Reactions that were catalyzed by (S)-indline-2-carboxylic acid (30 mol%) in CHCl3/MeOH 97:3 (v/v) showed high exo-selectivities (exolendo 91:9 similar to 99:1) and enantioselectivities (75 similar to 98% ee). In contrast, reactions catalyzed by L-proline (30 mol%) under similar conditions favored the endo-cycloadduct (83:27 similar to 99:1) with modest to good enantioselectivities (31 similar to 83% ee). Based on our studies, the diastereoselective mechanism of the L-proline-catalyzed reaction was found to involve the isomerization of the exo- to the endo-cycloadduct in the presence of L-proline. | |||||||||||||||||
| 資源タイプ（コンテンツの種類） | ||||||||||||||||||
| ISSN | ||||||||||||||||||
| 収録物識別子タイプ | ISSN | |||||||||||||||||
| 収録物識別子 | 0385-5414 | |||||||||||||||||
| 書誌レコードID | ||||||||||||||||||
| 収録物識別子タイプ | NCID | |||||||||||||||||
| 収録物識別子 | AA00663739 | |||||||||||||||||
| 他の資源との関係：URI | ||||||||||||||||||
| 識別子タイプ | URI | |||||||||||||||||
| 関連識別子 | http://www.heterocycles.jp/ | |||||||||||||||||
| 関連名称 | http://www.heterocycles.jp/ | |||||||||||||||||
| 権利 | ||||||||||||||||||
| 権利情報 | Copyright© 2010 The Japan Institute of Heterocyclic Chemistry | |||||||||||||||||
| 出版タイプ | ||||||||||||||||||
| 出版タイプ | AM | |||||||||||||||||
| 出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||||||||||||||
| WoS | ||||||||||||||||||
| URL | http://gateway.isiknowledge.com/gateway/Gateway.cgi?&GWVersion=2&SrcAuth=ShinshuUniv&SrcApp=ShinshuUniv&DestLinkType=FullRecord&DestApp=WOS&KeyUT=000281076100007 | |||||||||||||||||
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Suga, Hiroyuki, Arikawa, Tadashi, Itoh, Kennosuke, Okumura, Yukihisa, Kakehi, Akikazu, Shiro, Motoo, 2010, ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE IMINES WITH ACROLEIN CATALYZED BY L-PROLINE AND ITS DERIVATIVES: The Japan Institute of Heterocyclic Chemistry, 1669–1688 p.
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